Potassium Iodide → HCID 68488284, compound

Participants

Reaction Steps

To a solution of para-toluenesulfonic acid monohydrate (1.03 g, 5.40 mmol) in acetonitrile (11 ml) is added 4-(4′-amino-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-pyran-3,5-dione (0.65 g, 1.80 mmol), followed by stirring for 10 minutes at room temperature then cooling to 10° C. To this mixture is then added a second mixed solution of sodium nitrite (0.25 g, 3.60 mmol) and potassium iodide (0.76 g, 4.50 mmol) in distilled water (1.3 ml), and the mixture is then stirred at 10° C. for 20 minutes then at room temperature for 2 hours. Aqueous sodium bicarbonate solution is added until pH 9-10 is achieved, followed by dilution with ethyl acetate and washing with saturated aqueous sodium metabisulfite (20 ml). After additional extraction of the aqueous phase using ethyl acetate (×2) all organic fractions are combined, washed with distilled water and brine, then dried over anhydrous magnesium sulfate and concentrated in vacuo. This crude product is purified by flash column chromatography on silica gel (hexane/ethyl acetate 3:1 ratio) to yield an orange gum, which is triturated with hexanes to afford 4-(4′-iodo-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.413 g) as a white solid.

Provenance & Evidence